Permission To Quit

Solo Founder's Guide To Saving Their Time

One afternoon, just four months ago, when I was looking at my startup’s finance tracker and contemplating how to fund the next month, I suddenly received an email. Out of more than 10,000 applicants worldwide, eBay’s Circular Fashion Fund had shortlisted 24 companies, and Shezaar was one of them. A glimmer of hope for a founder who was about to quit.

At first I could not believe it. I read it twice. I thought for sure this was a mistake. Or maybe this was a spam email. But when the self-doubt settled, I was elated.

Two weeks of pitch prep and an amazing pitch later, I was not selected for the top eight. But, in a weird way, I was relieved.

Resilience Is Overrated

The cultural norm is that winners never quit and quitters never win, so we celebrate resilience and shame quitting. But most of the unhappiness, wasted years, stalled careers, and lost money come from people staying in losing positions long past the point where it stopped making sense.

I come from a third-generation family business. So, naturally I have a HUGE chip on my shoulder. I feel the constant need to prove myself and to seek external validation. Which is why quitting was never on the table.

So when the logic started showing me what I did not want to hear, I chose to ignore it. My fear of personal failure was far greater than the logic to just stop and salvage what I had. I told myself the answer was to work harder. So I worked harder. I worked through the holidays. I worked every weekend. But, had I tried to be objective, I would have made better decisions.

The Things I Was Refusing To See

There were three main issues, and they had been there from the start.

I did not love the industry. I did not love fashion. I loved the problem of textile waste. The two are not the same thing, and I had spent a year telling myself they were. Which meant I wasn’t the right person to solve the problem.

Every other fashion-tech founder I met could pitch their company using the latest styles, revered brands, and runway designers. Mine had a tone of “save these clothes.” I could not tell you the difference between Doên and Réalisation Par. But to kill the problem of waste, I had to sell fashion. To sell fashion, I had to understand it. And that was my biggest weakness.

The problem was real, but it was not urgent. Brands were managing their deadstock with patchwork solutions that worked well enough. There was no hair-on-fire moment yet. When the alternative is “deal with it later,” even a good solution loses to inertia.

And the last one: my customers, the shoppers, were spoilt for choice. The kind of buyer I was building for had thirty resale apps on her phone already. So, getting her attention required either viral organic momentum or a paid marketing budget. Without either, the unit economics did not make sense.

Now these might seem like surface-level problems that could have been solved by just being smart and scrappy. However, there were mistakes that I made along the way that made solving these nearly impossible. And I will post about them too.

The Strength To Kill

Sometime in the middle of that year, I had coffee with another founder. She was building her own thing, completely different from Shezaar, and at one point she said, casually, that if she did not hit a hundred paying customers in three months, she was quitting.

I remember thinking that was a horrible way to think about building a startup. How could you be committed to something if you had already imagined the version where you walked away?

But, I get it now. She had what Annie Duke calls kill criteria. Criteria that probably saved her a lot of time and money.

Annie Duke in her book Quit says that we quit too late, not too early. Grit and quit are not opposites. They are complementary skills, and most of us are great at one and terrible at the other.

The question is never “should I push through” versus “should I walk away.” The question is “is this still worth pushing through, given what I know now?” If your honest answer is yes, grit. If your honest answer is no, quit.

The reason this is hard is that your biases lie to you about the answer. The loudest one is sunk cost, telling you that you have come too far to stop. Underneath that is identity, telling you that founders do not quit. And the most seductive of all is optimism, telling you that next quarter the metrics turn.

So, having kill criteria does not mean you are not committed. It means you have given yourself the option to do something else if the evidence stops supporting the bet. And the criteria do not have to be about money. A hundred paying customers did not happen, but a thousand downloads did? That still works.

I walked out of that coffee shop thinking she was being defeatist. I had no kill criteria for Shezaar. I had a dream and a chip on my shoulder. So when the evidence started saying no, I had no agreement with myself about what no even looked like. So I just kept going.

What The Months Cost Me

Staying too long does not just cost you money. It costs you in ways that take longer to count. The people you stopped calling. The holidays you spent at your laptop instead of at the table. The body that kept score while you ignored it. The work you would have done if you had said no a quarter earlier and used those three months for something honest.

Most of what I lost was not the money. It was the months between knowing and saying.

What I Am Building Now

I quit Shezaar four months ago. I have spent the time since writing about my experience, building a network, and pitching half-baked ideas. I do not yet know what I am going to build next. But I know it will not start the way Shezaar did, with a build-first mentality.

And sometime soon I will write about the mistakes I made building Shezaar, mapped to the structural choices I am making this time so I do not make them again.

I have felt extremely embarrassed sharing this part of my story. But I am sharing it anyway.

For now, if you are reading this and you have evidence that is telling you to do something else or pivot, believe that evidence. And the smartest thing you can do for your future self is to decide what your kill criteria look like before you need them.